Madeline Benson (AB ’14) arrived at Harvard as a student of classical piano. But while at college, she discovered music directing and conducting through her experiences with the Radcliffe Pitches and HRDC shows. She fell in love with music directing for two reasons: her skills supported the work and she enjoyed it! “My musical toolkit was well-suited to what music directors have to do,” she smiles. “I love making stuff up on the fly, sight-reading, and the flexibility that theater demands from you.”

Despite majoring in Classical Civilizations while at the college, Madeline has found that her time studying at Harvard was also helpful for her career in a more abstract way than giving her hands-on music directing opportunities. “My experience with a lot of Harvard grads has been that what our concentrations gave us was a way of approaching a realm of thought or problem-solving,” she explains. “It’s about tackling big, complex ideas, breaking them down, and creating a plan or schema around them. Taking a big idea and breaking it down into smaller ideas… I think that’s also an artist’s process.”

She took her artist’s process to New York upon graduation. “I moved to New York and just tried to follow the momentum,” she recalls. “My first few years, I was a music assistant for a lot of shows in development. I did a lot of piano-related work, like rehearsal piano and playing for auditions, and a lot of transcribing sheet music.” Eventually, for Madeline, that freelance work led to more music directing opportunities and Broadway conducting opportunities, and now she finds herself in what she describes as a “big, dispersed cloud of music and theater.”

She’s had a fairly special run thus far in her career, making history as the youngest woman to direct on Broadway with Sara Bareilles’s musical WAITRESS in 2016. That experience was “unforgettable, so formative, and life-changing” for Madeline. “Not just because I got to conduct, but because I got to work with Sara Bareilles, who is a lifelong hero and a huge influence on my love of music and songwriting,” she recalls. “Watching how she worked in creative spaces was incredibly formative for me.” 

However, Madeline notes the disheartening feeling that comes along with making history like this. “Men have been conducting Broadway orchestras at even younger ages for a long time,” she says. “So, while it was really cool and I’m proud of it, it was also startling to realize that it was history-making. My only hope with all that is that it makes the gig seem even 5% more in reach for the next young woman who’s considering this path. Over time, that’s how we collectively break the glass ceiling. It’s not one person doing it all at once. It’s making it a little easier for the next person. There were many women before me doing that for me before I even got to New York. Someone has to be the first to make it easier for the next person.”

It’s that sort of dissonance that Madeline also finds within the Broadway industry as a whole. “Growing up, there was this magic in cast albums,” she grins. “It felt like there was this whole world and community happening in New York. The magic of having a CD at the time was an entry point into this hugely imaginative world… There was just always this aura of possibility and imagination around Broadway. It was irresistible to me, and the thought that I could take a step toward it or be part of it... I kind of put it up on this pedestal, thinking, ‘Well, that’s like making magic.’” 

But in reality, she’s found the industry a bit more complicated than her childhood imagination portrayed. “I think the biggest [challenge] in the theater industry right now is this preoccupation with what audiences want to see,” Madeline states. “On one level, I understand the impulse to craft work around that prompt— making musicals that have familiar styles of music or familiar stories, either through archetypes or literal existing intellectual property like well-known movies. Since COVID, Broadway is still rebuilding its audience, and tourism is crucial, so adaptations of existing IP can be wonderful. By no means does that mean it’s not a creative venture. However, I think what really grips audiences is when a show knows itself well enough to say [confidently]—instead of asking, ‘Do you like this?’ telling them, ‘You're gonna like this!’"

Aside from industry-wide complexities, Madeline also faces some more personal challenges as she works. “The biggest challenge of my career has been that music directors are in this beautiful, sacred position of facilitating and interpreting the work of composers, directors, and other artists,” Madeline explains. “Those relationships are the most intricate, challenging, and rewarding aspects of the job. Every composer is different, and what they look for in their music director can vary a lot. Directors change so much case by case, and that sort of adaptability to walk into a new collaboration and build it is really intimate and rewarding, but it can feel like dating. Everyone is kind of trying to find the people that make them feel most safe and creative. I believe any artist who's vulnerable enough to share their work deserves to be surrounded by really trusted people. I take the music directing role very seriously because… it's about supporting people well.” 

As much as she works supporting others in bringing their creative visions to fruition, Madeline is also currently embarking on her own solo journey right now. She’s in the process of recording an album of her own music, with the first and second singles already out (listen to them here!). “It's been a long time coming for me,” Madeline smiles. “I think we all have many facets to our artistic identities, but I may have gotten a little fearful or complacent in being in this supportive facilitator role… So, I’m releasing all this music, and it feels incredibly unknown and new.”

With her many years of experience, Madeline has some wonderful advice for young, aspiring music directors. First, you must “know your toolkit and own it.” This is because, Madeline says, “Music directors are good at different things, and something that’s been humbling but valuable as I’ve gotten a few years under my belt is realizing there are some jobs I’m just not the best fit for as a music director… Instead of being a generalist, I think it can help to say, ‘This is what I really, really specialize in,’... Knowing yourself is good. That doesn’t limit you.”

Her other piece of advice is specifically for female music directors looking to enter the musical theater industry. “There's a real influx of female music directors and conductors in the last few years, which is wonderful, and I hope it increases forever,” Madeline pauses, “[But] I think it's worth keeping an eye on this question of facilitating and supporting because women are really good at those things. It makes total sense why women are great conductors and music directors. That's not even a question… But women shouldn’t settle for being in close proximity to the creative process if they’re the ones who should actually be in the driver's seat, thinking it all up.”

Listen to Madeline’s music here.